Read Time = 4 minutes

This April I got a message from the Founder of a services business who was struggling to generate conversations over cold email.

They just raised a Seed round but pipeline was shrinking and referrals were starting to run dry.

Naturally, he wanted help driving more pipeline.

But first, he had to find message-market fit.

We jumped on a call and I asked my typical questions around who they were targeting, what they were saying and how it was working.

Then I heard a common problem shared across many start-up Founders.

You’re sending LOTS of emails but it’s not leading to replies or revenue.

Typically, this struggle comes down to:

1. Targeting the wrong people

2. Targeting the right people with the wrong message

I dove in and sure enough the challenges they experienced were a result of both.

Over the next week we rebuilt their GTM sequence by focusing on:

ONE persona and ONE problem.

It worked - 6 weeks later they generated $345k in pipeline from the campaign.

More importantly, they landed $78k in revenue from mid-market customers.

In the rest of this post, I’ll share how I build outbound campaigns that drive meetings and meaningful pipeline:

Who to Target:

Imagine you’re selling a part-time accounting service to the office of the CFO.

Start by mapping buyer personas on a matrix like the one below.

• Green = experiencing pain point, decision maker

• Yellow = experiencing pain point, influencer

• Red = not experiencing pain point, not a fit

Then pick ONE persona that falls into the green zone like “CFOs”.

It’s OK if your initial hypothesis is off, I’ll explain how to pivot later.

Where to Prospect:

Where you prospect should tie directly into what you say.

Lets build off our example of targeting CFOs, selling your accounting services.

Some signals you might look for that indicate fit and timing include:

• CFOs at companies hiring mid/low level accounting roles

• CFOs at companies that have recently taken on an investment

• CFOs at companies that are growing very quickly

Tools like Clay and ZoomInfo can build lists and scrape data automatically.

Now for the hard part, turning your research into compelling messaging…

What to Say:

My recommendation is to segment your campaigns by persona + problem.

Signals are meant to help you personalize.

Here’s how I like to structure my initial outreach:

• Relevance: signal that aligns to the problem you solve

• Claim: align the problem to your buyers responsibilities

• Evidence: show or share why this is a problem for many

• Impact: outcome you have helped others achieve

• CTA: low friction, interest based

In this example, the Persona = CFO. The Problem = Inaccurate ARR reporting.

Measuring Success:

Before you start emailing, it’s important to set constraints around execution.

A common variable that I like use = emails sent.

Typically, ~250 emails for each message in a sequence is sufficient volume.

Below are KPI benchmarks you can use for measure effectiveness.

If you’re below these thresholds here are a few places to dig in:

• Open rate = subject lines, first sentence, name/image

• Reply rate = readability, relevance and research

• Positive replies = signals used, matching problems + persona

• Bounce rate = domain health, contact data, daily volume

TL;DR:

To find message-market fit focus on ONE persona and ONE problem.

For our example selling accounting services, this might look like:

• Iteration 1 = CFOs backed by PEs, struggling with ARR reporting

• Iteration 2 = CFOs at high growth company, stuck using manual processes

• Iteration 3 = CFOs with small teams, concerned over passing audits

Each of these can be 2-3 week campaigns or ~250 emails sent.

If your initial hypothesis isn’t producing results referenced above, pivot.

It might be time to target a new persona pitching a different problem.

Until next Thursday,

TSG

P.S. I reply to all emails.